DE3204079A1 - Verfahren zur herstellung von hydroxydiphenylen - Google Patents
Verfahren zur herstellung von hydroxydiphenylenInfo
- Publication number
- DE3204079A1 DE3204079A1 DE19823204079 DE3204079A DE3204079A1 DE 3204079 A1 DE3204079 A1 DE 3204079A1 DE 19823204079 DE19823204079 DE 19823204079 DE 3204079 A DE3204079 A DE 3204079A DE 3204079 A1 DE3204079 A1 DE 3204079A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- weight
- diphenyl
- pressure
- mixture
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 81
- 239000002253 acid Substances 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 44
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 34
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 33
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 26
- 239000011541 reaction mixture Substances 0.000 claims description 18
- 238000002156 mixing Methods 0.000 claims description 15
- CGEXUOTXYSGBLV-UHFFFAOYSA-N phenyl benzenesulfonate Chemical class C=1C=CC=CC=1S(=O)(=O)OC1=CC=CC=C1 CGEXUOTXYSGBLV-UHFFFAOYSA-N 0.000 claims description 15
- 239000000243 solution Substances 0.000 claims description 15
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 14
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims description 13
- 150000001447 alkali salts Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 238000006386 neutralization reaction Methods 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- 238000010790 dilution Methods 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- 239000004305 biphenyl Substances 0.000 description 18
- 235000010290 biphenyl Nutrition 0.000 description 16
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
- 125000006267 biphenyl group Chemical group 0.000 description 13
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 9
- 235000002639 sodium chloride Nutrition 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 description 8
- 150000003460 sulfonic acids Chemical class 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- -1 diphenyl sodium sulfonates Chemical class 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 4
- 238000006277 sulfonation reaction Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000007664 blowing Methods 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 3
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229910001026 inconel Inorganic materials 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000005185 salting out Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLHGZXJNKKTXGY-UHFFFAOYSA-N 2,3,4-triphenylcyclohexa-1,5-diene-1,4-diol Chemical compound C=1C=CC=CC=1C1(O)C=CC(O)=C(C=2C=CC=CC=2)C1C1=CC=CC=C1 XLHGZXJNKKTXGY-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000006887 Ullmann reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 150000008107 benzenesulfonic acids Chemical class 0.000 description 1
- CXJVMJWCNFOERL-UHFFFAOYSA-N benzenesulfonylsulfonylbenzene Chemical compound C=1C=CC=CC=1S(=O)(=O)S(=O)(=O)C1=CC=CC=C1 CXJVMJWCNFOERL-UHFFFAOYSA-N 0.000 description 1
- UBXYXCRCOKCZIT-UHFFFAOYSA-N biphenyl-3-ol Chemical compound OC1=CC=CC(C=2C=CC=CC=2)=C1 UBXYXCRCOKCZIT-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000010309 melting process Methods 0.000 description 1
- 229910001463 metal phosphate Inorganic materials 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis by substitution of SO3H groups or a derivative thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823204079 DE3204079A1 (de) | 1982-02-06 | 1982-02-06 | Verfahren zur herstellung von hydroxydiphenylen |
| US06/459,738 US4467123A (en) | 1982-02-06 | 1983-01-20 | Process for the preparation of alkali metal diphenylates and free hydroxydiphenyls |
| DE8383100614T DE3360174D1 (en) | 1982-02-06 | 1983-01-25 | Process of synthesis of hydroxydiphenyls |
| EP83100614A EP0085883B1 (de) | 1982-02-06 | 1983-01-25 | Verfahren zur Herstellung von Hydroxydiphenylen |
| JP58014692A JPS58135831A (ja) | 1982-02-06 | 1983-02-02 | ヒドロキシジフエニル類の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19823204079 DE3204079A1 (de) | 1982-02-06 | 1982-02-06 | Verfahren zur herstellung von hydroxydiphenylen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3204079A1 true DE3204079A1 (de) | 1983-08-18 |
Family
ID=6154956
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19823204079 Withdrawn DE3204079A1 (de) | 1982-02-06 | 1982-02-06 | Verfahren zur herstellung von hydroxydiphenylen |
| DE8383100614T Expired DE3360174D1 (en) | 1982-02-06 | 1983-01-25 | Process of synthesis of hydroxydiphenyls |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8383100614T Expired DE3360174D1 (en) | 1982-02-06 | 1983-01-25 | Process of synthesis of hydroxydiphenyls |
Country Status (4)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4804788A (en) * | 1986-11-07 | 1989-02-14 | Kureha Kagaku Kogyo K.K. | Preparation process of 4,4-dihydroxybiphenyl |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4546207A (en) * | 1983-02-28 | 1985-10-08 | General Electric Company | Process for preparing anhydrous salts of dihydroxyaromatic compounds |
| DE3801943A1 (de) * | 1988-01-23 | 1989-07-27 | Basf Ag | Verfahren zur herstellung von 4,4'-dihydroxybiphenyl |
| DE3831712A1 (de) * | 1988-09-17 | 1990-03-22 | Basf Ag | Verfahren zur herstellung von 4,4"-dihydroxyterphenyl |
| DE3840618C1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1988-12-02 | 1990-03-15 | Bayer Ag, 5090 Leverkusen, De | |
| DE19624202A1 (de) * | 1996-06-18 | 1998-01-02 | Bayer Ag | Verfahren zur Herstellung von 4-Hydroxydiphenyl |
| DE10040165A1 (de) * | 2000-08-17 | 2002-02-28 | Bayer Ag | ortho-Phenylphenolat-Konzentrate |
| CN100497280C (zh) * | 2006-01-17 | 2009-06-10 | 沈阳化工研究院 | 一种对苯基苯酚的制备方法 |
| CN116730803A (zh) * | 2023-06-28 | 2023-09-12 | 锦州三丰科技有限公司 | 一种联苯二酚的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB649945A (en) * | 1947-04-18 | 1951-02-07 | Ciba Ltd | Manufacture of oxy-compounds of the naphthalene series |
| FR1108177A (fr) * | 1953-07-09 | 1956-01-10 | Sterling Drug Inc | Procédé de production de bêta-naphtol |
| JPS5111618B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-05-02 | 1976-04-13 | ||
| JPS4916417A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1972-05-22 | 1974-02-13 | ||
| JPS582838B2 (ja) * | 1975-12-04 | 1983-01-18 | リソウカガクコウギヨウ カブシキガイシヤ | カンネツセイコウハンインサツヨウゲンシ |
| US4243822A (en) * | 1979-08-31 | 1981-01-06 | Buffalo Color Corporation | Process for the manufacture of 4,4' dihydroxydiphenyl |
| JPS5657728A (en) * | 1979-10-17 | 1981-05-20 | Hodogaya Chem Co Ltd | Preparation of 4,4'-dihydroxybiphenyl |
-
1982
- 1982-02-06 DE DE19823204079 patent/DE3204079A1/de not_active Withdrawn
-
1983
- 1983-01-20 US US06/459,738 patent/US4467123A/en not_active Expired - Fee Related
- 1983-01-25 EP EP83100614A patent/EP0085883B1/de not_active Expired
- 1983-01-25 DE DE8383100614T patent/DE3360174D1/de not_active Expired
- 1983-02-02 JP JP58014692A patent/JPS58135831A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4804788A (en) * | 1986-11-07 | 1989-02-14 | Kureha Kagaku Kogyo K.K. | Preparation process of 4,4-dihydroxybiphenyl |
| USRE33779E (en) * | 1986-11-07 | 1991-12-24 | Kureha Kagaku Kogyo K.K. | Preparation process of 4,4-dihydroxybiphenyl |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3360174D1 (en) | 1985-06-20 |
| JPS58135831A (ja) | 1983-08-12 |
| EP0085883B1 (de) | 1985-05-15 |
| JPS6338334B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-07-29 |
| EP0085883A1 (de) | 1983-08-17 |
| US4467123A (en) | 1984-08-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0085883B1 (de) | Verfahren zur Herstellung von Hydroxydiphenylen | |
| DE3240805A1 (de) | Verfahren zur herstellung von hydroxy-phenoxy-alkancarbonsaeuren | |
| DE2648300A1 (de) | Verfahren zur herstellung von salzen der 3,3-dimethyl-2-oxobuttersaeure | |
| DE1543637C3 (de) | Verfahren zur Herstellung farbloser kristalliner Diphenylsulfone | |
| DE3031094C2 (de) | Verfahren zur Herstellung eines Alkalisalzes des 4,4'-Dihydroxydiphenyls | |
| DE3840618C1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| EP0083555B1 (de) | Verfahren zur Herstellung von p-Nitrotoluol-2-sulfonsäure | |
| EP0283898A2 (de) | Verfahren zur Herstellung von Aryldiazidsulfonsäuren | |
| EP0816318B1 (de) | Verfahren zur Herstellung von 4-Hydroxydiphenyl | |
| EP0066770B1 (de) | Verfahren zur Herstellung von 3-Hydroxybenzoesäure | |
| EP0115299B1 (de) | Verfahren zur gleichzeitigen Gewinnung von 4-Hydroxydiphenyl und 4,4'-Dihydroxydiphenyl | |
| DE3226392C2 (de) | Verfahren zur Herstellung von 4,4'-Diphenyldisulfonsäure oder von deren Monokaliumsalz | |
| DE1668966B1 (de) | Verfahren zur gleichzeitigen Herstellung von 2,6-Dimethyl-phenol und 4-tert.-Butylphenol | |
| EP0214544B1 (de) | Verfahren zur Herstellung von 1-Aminonaphthalin-4-sulfonsäure (Naphthionsäure) | |
| DE19651040C2 (de) | Verfahren zur Herstellung von 2-Amino-5-alkyl-phenolen | |
| EP0143750A2 (de) | Verfahren zur Herstellung von 4-Nitrotoluol-2-sulfonsäure | |
| EP0038999B2 (de) | Verfahren zur Herstellung von 2-Chlor-5-formylbenzolsulfonsäure | |
| DE2703919B1 (de) | Verfahren zur Herstellung von p-Nitroso-diphenylhydroxylaminen | |
| DE2210916C3 (de) | Verfahren zur Herstellung von Dibrompropyläthern hochhalogenierter Phenole | |
| DE3118903A1 (de) | Verfahren zur herstellung von 1-benzoylamino-8-hydroxy-naphthalin-4.6.-disulfonsaeure (benzoyl-k-saeure) | |
| DE69703279T2 (de) | Verfahren zur herstellung von m-hydroxyalkylbenzol | |
| DE1951797A1 (de) | Verfahren zur Herstellung von Resorcin | |
| DE2028596A1 (de) | Verfahren zur Herstellung einer Mischung von Benzoldisulfonsaure und Benzolmonosul fonsaure oder Toluolmonosulfonsaure | |
| DE4201801A1 (de) | Verfahren zum reinigen von roher 4,4'-diamino-1,1'-dianthrachinonyl-3,3'-disulfonsaeure und ihren salzen | |
| DE2034410A1 (de) | Verfahren zur Herstellung von Resor ein |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |